Chicago Lake Michigan Tours

The Lake Michigan Sunset Cruise departs near the DuSable (Michigan Avenue) Bridge on Wendella's world class tour boats. The Cruise will navigate from the Chicago River, through the Chicago Lock and out onto Lake Michigan. Watch the sun slowly set behind the city from the tranquil waters of Lake Michigan on this serene and romantic cruise.

Enjoy Chicago’s iconic skyline with an exciting speedboat Tour on Lake Michigan. Departing from Navy Pier, the Lakefront Speedboat Tour is the best way to view Chicago from the water. Seadog offers fun for the whole family (and the dog, too!) combining an exciting speedboat ride along the shoreline with informative and amusing descriptions of the world-famous Chicago skyline!

Join us for an unforgettable afternoon on Lake Michigan with a Signature Chicago Lunch Cruise. Whether it’s a family outing or a meal with friends, upgrade your lunch with a chef-prepared buffet and sweeping views of Chicago’s iconic landmarks, such as Adler Planetarium and Navy Pier. This fun and relaxed lunch cruise experience is complete with live DJ entertainment, a fully stocked cash bar, dancing, and games on the open-air decks and indoor spaces. Set sail for a one-of-a-kind afternoon that is as scenic as it is delicious!

Set sail on our flagship vessel, where style meets comfort in a Tiki Chic atmosphere. Your adventure begins on the iconic Chicago Riverwalk, where you’ll board a beautifully appointed boat featuring two climate-controlled decks, two full bars, two bathrooms, and both indoor and outdoor viewing areas—perfect for soaking in the sights no matter the weather. As you sip a refreshing beverage, enjoy the rare experience of transiting the historic Chicago Locks—a must-see for locals and visitors alike. Once you glide into the open waters of Lake Michigan, you’ll be treated to breathtaking views of Chicago’s world-famous skyline, framed by the gentle breeze and city lights. Looking to elevate your cruise? Upgrade to the exclusive Admiral’s Lounge, where you’ll enjoy top-shelf spirits, including selections from the Captain’s Private Reserve, all in a more intimate, upscale setting. This is more than just a boat ride—it’s a uniquely Chicago experience you won’t forget!

Paddle the calm, clean and turquoise waters of Lake Michigan at your own pace. Kayak the lakefront scenery in downtown Chicago on your own personal kayak, taking in the city skyline and lake views. Pull off at a nearby beachfront and enjoy time on the sand before paddling further.

Set sail for a memorable experience on Lake Michigan with a Signature Chicago Brunch Cruise that is as scenic as it is delicious! You'll savor a chef-prepared buffet and bottomless mimosas while in our comfortable indoor areas. Marvel at unparalleled views of Chicago’s iconic landmarks, such as Willis Tower and Navy Pier from inside or enjoy fresh breezes on the open-air decks. This fun-filled brunch cruise experience for all ages is complete with lively DJ entertainment, dancing, games, and a fully stocked cash bar. Elevate your weekend plans with a one-of-a-kind brunch cruise on the water!

Enjoy a picturesque day dining on Lake Michigan with our Premier Chicago Brunch Cruise. You’ll indulge in a chef-prepared buffet meal featuring savory and sweet classics, bottomless mimosas, top-notch service, and breathtaking views of the city skyline, all while our live DJ sets the mood. Capture photos in front of Chicago’s famous landmarks, such as Adler Planetarium and Willis Tower, and soak in the sweeping panoramic views from the comfort of our comfortable indoor spaces and open-air decks. Join us for a spectacular brunch cruise that will not be forgotten. Includes 2-hour brunch cruise on Lake Michigan Chef-prepared buffet-style dining Bottomless mimosas (must be 21 or older with valid ID) Spectacular views of the Chicago skyline including the Willis Tower and Adler Planetarium DJ curated music Guaranteed table for your party size Complimentary coffee, hot tea, and iced tea

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. Make the experience your own. The flexibility of a private charter allows customization of virtually any aspect of the sailing adventure from guest list to music selection to sailing route. Three departure times offered daily. This experience is not meant to be an in-depth guided tour; however, our captain is always happy to point out interesting sights with anecdotes and historical information. Just ask you captain. Looking for a sunset sail, see our other product listing "Come Sailing with us at Navy Pier - Sunset Sail on Lake Michigan". Looking to watch the Navy Pier Fireworks from a private sailing charter, see our other product listing "Come Sailing with us at Navy Pier - Saturday Fireworks Sail". All charters are NON-SMOKING experiences.

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. Make the experience your own. The flexibility of a private charter allows customization of virtually any aspect of the sailing adventure from guest list to music selection to sailing route. This experience is not meant to be an in-depth guided tour; however, our captain is always happy to point out interesting sights with anecdotes and historical information. Just ask you captain. Looking for daytime sailing, see our other product listing "Come Sailing with us at Navy Pier - Sail Beautiful Lake Michigan". Looking to watch the Navy Pier Fireworks from a private sailing charter, see our other product listing "Come Sailing with us at Navy Pier - Saturday Fireworks Sail". All charters are NON-SMOKING experiences.

Four days to enjoy the beautiful scenery of the three major lakes in the Great Lakes region of the US, all of which are located in Lake Michigan in the US. Four famous lakeside cities: Milwaukee and Traverse City along Lake Michigan, Green Bay along Green Bay, and Sault Ste. Mackinac Island, which was once selected as one of the top ten most beautiful islands in the world and known as the treasure of the Great Lakes in North America; Sleeping Bear Dunes National Lakeshore Scenic Area with beautiful beaches. Room Details All hotel rooms are based on two Full / Double beds or one King/Queen bed depends on what rooms are availiable at the hotel on the day. The maximum occupancy per room is four travelers. One Room Selection If you are a party of more than four guests or desire to have separate rooms, please create separate bookings. Avoid traveling in a different bus? If you have more than one booking, please provide all confirmation numbers once your bookings are complete.

JT and the team ensures a seamless, guided experience, whether you're a seasoned angler or a first-timer. Enjoy satellite entertainment and hi speed wifi for those last minute video conference calls. Our commitment to comfort, elegance, and excellence sets us apart in every detail. From sunrise departures to golden hour returns, every moment is tailored for exclusivity. Whether you're celebrating a milestone or escaping the ordinary, we make every trip unforgettable. Discover what it means to fish luxuriously—reserve your elite charter today.

Walk beneath Chicago’s soaring skyline, hear its hidden stories, then see it shimmer from the water on a lake cruise. From the iconic Bean to the legendary theatre district, this tour brings the city’s spirit to life—one step and wave at a time. Highlights: • Discover downtown Chicago on foot with a 5-Star Private Guide leading the way • Cruise Lake Michigan with included tickets and audio commentary onboard • See breathtaking skyline views and snap iconic photos from the water • Learn the city’s best-kept secrets through fascinating stories and history • Get tailored recommendations on top spots to eat, visit, and explore next Did you know there’s a sculpture in Chicago that reflects the whole skyline? With Rosotravel’s private tour, you'll walk through the city’s most iconic spots, then see it all again from the water on a relaxing lake cruise. It's a fun, personal way to experience the best of Chicago in just a few hours.Reserve your spot ow!